Experiment 4: Extraction

Ajay Chandrasekaran
CHEM 2411-6, TA: A. Tran, 9/29/21
Purpose: To learn the laboratory technique of extraction through a two part experiment. The
purpose of the first part of the experiment was to understand the effect of pH on the solubility of
an indicator while the purpose of the second part of the experiment was to separate and identify
two organic unknowns in a solution.
Procedure: For the first part of the experiment, 5mL of chloroform (CHCl3) was added to a
medium test tube followed by 2mL of a basic solution of 2,6-dichloro-indophenol. The color was
observed once now, once after shaking the test tube (stopper added) once, and finally another
time after vigorously shaking the test tube. Next, 4mL of 1N NaOH was added and the same
sequence of color analysis was done as before. It is important to note that the test tube was
vented appropriately between shaking to relieve pressure.
The second part of the experiment was split into two steps and involved the laboratory
technique of extraction followed by back-extraction. Extraction is performed using a separatory
flask and the solvents of interest. The solvent that is less dense sits on top of the solvent that is
more dense. In this experiment, the organic layer sits on top while the aqueous layer sits on the
bottom. The aqueous layer, which could be either neutral, base, or acid, is separated from the
organic layer by draining it into another test tube by carefully opening and closing the stopcock
on the separatory flask. The extracted aqueous layer can then be further purified using a
technique called back extraction. In back extraction, ethyl acetate is used to extract any organic
layer that might have gotten into the aqueous sample of either neutral, base, or acid component.
The first step of the second part of the experiment involved the isolation of a 5mL
solution containing two unknowns in ethyl acetate into its base, neutral, and acid component. To
achieve this, first the unknown was extracted in a separatory flask three times using 1 mL
portions of 10% HCl to isolate the basic component. After shaking the solution, the basic
component becomes the more dense aqueous layer allowing us to isolate it from the less dense
yellowish organic layer on the top. This aqueous layer was collected into a test tube labelled
“basic component” while the remaining organic layer was collected into a test tube labelled
“organic solution”. The resulting basic component was then back extracted three times using 1
mL portions of ethyl acetate to purify it further followed by pouring the aqueous layer into the
basic component test tube and the organic layer into the organic solution test tube. The remaining
unknown organic solution was extracted three more times, but this time using 1 mL portions of
10% NaOH to isolate the acidic component. This was poured into a new tube labelled “acidic
component”. The remaining organic layer after this extraction is actually the neutral component
which was poured into another test tube called “neutral component”. The extracted acidic
component was back-extracted three times using 1mL portions of ethyl acetate similar to the
back extraction performed for the basic component but this time with the aqueous layer poured
in the acidic component test tube and the organic layer poured into the neutral component test
tube.
 The second step of the second part of the experiment involved purifying the neutral and
basic components, followed by identifying them using melting point analysis. The neutral
component is in a solution of ethyl acetate, which has a small amount of residual water. In order
to remove this water, a small amount of solid magnesium sulfate is added and the test tube is
swirled and allowed to sit for 10 minutes. Next, the neutral component is slowly decanted into a
tared round-bottom flask. The solvent is then evaporated using a rotary evaporator which gives
us a solid neutral component to identity by melting point analysis and also the yield. A similar
process is performed for the basic component. Before drying the basic component with
magnesium sulfate though, a couple of other steps need to be performed. The basic solution is in
a solution of aqueous acid, which can’t be evaporated using a steam bath and therefore another
process of extraction must take place. Before this, enough 10N NaOH was added into the
solution until it appeared cloudy, indicating that it was basic. Similar to extractions before, three
1 mL portions of ethyl acetate were used. This time however, the organic layer (top layer) is the
basic component. But since the basic component is still now in a solution of ethyl acetate, the
steps involving magnesium sulfate as mentioned for the neutral component are done, followed by
melting point analysis and yield calculation to identify it.
Calculations:
1) Calculation of Mass of Unknown
Mass of Unknown = Amount of Sample (mL) * Concentration of Sample (g/mL)
Mass of Unknown = 5 mL * 20 g/mL = 5ml * 20g/1000mL
Mass of Unknown = 0.10g of unknown in ethyl acetate
2) Calculation of Yield
Yield = (Observed Recovery / Mass of Unknowns) * 100%
Yield = (0.15g / 0.10g) * 100% = 150%
Results:
Observations of Extracted Components
Extracted Component Yield (g) Yield (%) Appearance Melting point (C)

Acid N/A N/A N/A N/A

Base 0.06 60% Dull White N/A

Neutral 0.15g 150% Orangish-Yellow N/A

Discussion: Extraction is the transfer of a solute from one solvent to another. When a solute is
placed in two immiscible solvents and shaken, it will distribute itself between the two liquid
phases in such a manner as to define a constant K, the distribution coefficient. This constant can
be used to back up why three extractions were performed in every step involving extraction or
back-extraction in this lab. As seen from an example calculation in Appendix B, the more
separated and individual extractions done, the more pure and more quantity you get of a desired
product. Multiple extractions with small quantities of solvent are more efficient than a single
extraction with a large quantity of solvent. Overall, Extraction is a common laboratory technique
that can be used to isolate components of an unknown. This can then be used to identify the
unknown with the aid of another common laboratory technique called melting point analysis,
where the melting point of the components are observed and compared with known values to
identify an unknown compound.
The purpose of the first part of the experiment was to understand the background
knowledge needed for extraction by observing the effect of pH on the solubility of an indicator
based on color changes in the organic and aqueous layers of a solution. As components were
added into the solution, a color change was observed, indicating the movement/presence of either
the organic or aqueous layer (Appendix C). In the original mixture, the aqueous layer
(2,6-dichloro-indophenol) was charged while the organic layer was non-polar (chloroform),
hence the two layers were immiscible and separate. The color indicator was dissolved in the
aqueous layer (basic pH), and was blue in the original mixture. This indicates that the color
indicator is charged and therefore is most soluble in a charged solvent (like dissolves like). The
organic layer in the original mixture was clear because the charged indicator was not soluble in
the non-polar organic layer. The addition of HCl to the solution protonated the base in the
aqueous layer, changing the aqueous layer from charged to neutral. The color indicator was still
in the aqueous layer but the color had changed from blue to a bright red when the solution was
undisturbed. The solution was mixed and the layers were now more difficult to distinguish
because the two layers were now both nonpolar and thus miscible. The indicator turned orange
and fell to the bottom of the test tube now that both layers were neutral and mixed. The addition
of NaOH then deprotonated the aqueous layer once again, making it charged with a basic pH and
causing the two layers to separate once again due to immiscibility. A little bit of blue color
formed between the two layers showing the indicator moving back towards the charged aqueous
layer that the indicator was more soluble in. The solution was then shaken and the final coloring
of the layers showed a clear, bottom organic layer, and a blue aqueous layer on top. The
indicator was now soluble in the charged aqueous layer while the clear and neutral organic layer
was below.
The purpose of the second part of the experiment was to extract the unknown solution
into basic, neutral, and acidic components, purify them, and finally identify them using melting
point analysis. Since we were told that our unknown solution was basic, no analysis was done for
the acidic component since the results would have been irrelevant. Therefore, only the basic and
neutral components were purified and conducted melting point analysis on as can be seen in
Results. The basic component had a yield of 60% while the neutral component had a yield of
150%. Based on these numbers it is reasonable to say that the neutral component was not as very
pure and might have been contaminated leading to an observed extra yield. In contrast, the basic
component could be pure, but not all the basic components are being represented. When
analysing what could have caused these results, it is important to understand that extraction is a
process done with the human hand and eye and therefore is highly prone to human error. It is
very hard to tell when all the aqueous layer is extracted from the extraction flask and even harder
to precisely close the stopccok when the desired layer is extracted. To battle this, a pipet could be
used after every round of extraction to put back any of the undesired layers back into the
extraction apparatus to be extracted further. One other mitigation effort that could be done is to
simply increase the number of extractions done as it is proven to produce a purer product
(Appendix B).
No melting point analysis was done for the basic or neutral components due to some
difficulties. For both components, only very little solid was able to be put inside the melting
point tubes for melting point analysis. This was due to the difficulty of crushing the solid
extracted after rotary evaporation and inserting it into the small radius hole of the melting point
tube. Although it was thought to be sufficient to observe the melting point, there was little to
view through the view hole on the melting point apparatus. Both tubes containing each
component appeared to melt as soon as it was heated. This could either be due to just not being
able to sufficiently observe the little solid present or that the components were not very pure. In a
perfect world, more solid would have been able to be put into the melting point tubes for the two
components, melting points observed, and components identified using Appendix A. Better tools
could have been used to crush the solid components, or maybe a different melting point
apparatus with larger melting point tubes could have been used.
To conclude, although extraction is a proven laboratory technique that can be used to
isolate components of an unknown, the application of it requires precise handling and care to
produce significant results. Once this has been achieved, further laboratory techniques can be
used to even identify the unknown. One example of this using melting point analysis.
Appendix A: Possible Unknowns

Appendix B: Significance of Multiple Extractions

Appendix C: Part 1 Results (Colors of Organic & Aqueous Layers)

Event Organic Layer Color Aqueous Layer Color

Organic Mixture Clear Blue

+ 4mL of 1N HCl Clear Red

Shake Vigorously Orange Clear

+ 4mL of 1N NaOH Slight Blue Slight Blue

Shake Vigorously Clear Clear